Synthesis and evaluation of aminocyclopentitol inhibitors of β-glucosidases

被引：38

作者：

Boss, O ^{[1
]}

Leroy, E ^{[1
]}

Blaser, A ^{[1
]}

Reymond, JL ^{[1
]}

机构：

[1] Univ Bern, Dept Chem & Biochem, CH-3012 Bern, Switzerland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 02期

关键词：

D O I：

10.1021/ol991252b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] (1R,2S,3S,4R,5R)-4-Amino-5-(hydroxymethyl)cyclopentane-1,2,3-triol 1, prepared from D-glucose, inhibits beta-glucosidases from Caldocellum saccharolyticum (K-i = 1.8 x 10(-7) M) and from almonds (K-i = 3.4 x 10(-6) M). Inhibition is not influenced by N-ethylation (--> 15) but is strongly reduced upon N-acetylation (--> 12). Inversion of stereochemistry at C(5) (--> 14) has little effect on inhibition of beta-glucosidases. These experiments suggest that 1 acts as an analogue of a protonated beta-glucoside.

引用

页码：151 / 154

页数：4

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